Dear Label_Name,

Greetings! I hope you are well.

I am writing on behalf of an international publishing house, Science and Education Publishing, USA (http://www.sciepub.com).

Science and Education Publishing (SciEP) is a multidisciplinary open access publisher of Journals covering the fields of Science, Technology and Medicine. All SciEP publications are subject to high-quality peer review, editorial and production processes and are freely available online.

Welcome to the April, 2013 edition of SciEP newsletter, providing monthly summaries of articles on science & education related topics of interest to scientist and professionals. The mission of our journals is to provide an open access forum for publishing new findings on issues pertinent to scientific and academic field. We also invite you to submit original research papers, review articles, short reports, or case studies are considered for publication in our Multidisciplinary Journals.

American Journal of Public Health Research
DOI: 10.12691/ajphr-1-1-3

The Implementation of a Tele-Homecare System with Service Oriented Architecture and HL7 Message Transmission Standard
Ching-Sung Wang

American Journal of Medical and Biological Research
DOI: 10.12691/ajmbr-1-1-2

The Influence of Ethanol on Pyruvate Kinases Activity in Vivo, in Vitro, in Silico
Lelevich Sergey Vladimirovich, Khrustalev Vladislav Victorovich, Barkovsky Eugene Victorovich, Shedogubova Tatyana Aleksandrovna

American Journal of Medical Sciences and Medicine
DOI: 10.12691/ajmsm-1-1-1

Clinical and Histological Features in Wegener Granulomatosis
Li Cavoli Gioacchino, Passantino Rita, Bono Luisa, Tortorici Calogera, Ferrantelli Angelo, Giammarresi Carlo, Rotolo Ugo

American Journal of Infectious Diseases and Microbiology
DOI: 10.12691/ajidm-1-1-2

The Curse of Lymphatic Filariasis: Would the Continual Use of Diethylcarbamazine Eliminate this Scourge in Papua New Guinea?
Anne Lanham, Lillian Mwanri

We have released issues of some journals on February 2013.
American Journal of Public Health Research
American Journal of Medical Sciences and Medicine
American Journal of Medical and Biological Research
American Journal of Pharmacological Sciences
American Journal of Clinical Medicine Research
American Journal of Nursing Research
American Journal of Cancer Prevention
American Journal of Medicine Studies
American Journal of Infectious Diseases and Microbiology
American Journal of Cardiovascular Disease Research
American Journal of Biomedical Research
American Journal of Mechanical Engineering
American Journal of Microbiological Research
Journal of Preventive Medicine
American Journal of Food and Nutrition
American Journal of Hypertension Research
American Journal of Sports Science and Medicine
Journal of Cancer Research and Treatment
American Journal of Zoological Research
Journal of Biomedical Engineering and Technology
American Journal of Microbiological Research
Biomedical Science and Engineering

We are pleased to announce that submissions are now being accepted for peer review for all the journals across all our subject areas in SciEP.

Please submit your manuscript via our online submission system:
http://www.sciepub.com/author/signin

To unsubscribe from our mailing list, please click on the following link: unsubscribe

I am looking forward to hearing from you.

Kind regards,

David Rain
Email:join@sciepub.com
Science and Education Publishing (http://www.sciepub.com)

Copper-Catalyzed Hydroamination of Terminal Alkynes by Combining N-fluorobenzenesulfonimide and H2O: Synthesis of β-amino Substituted Styrenes

Tony Wheellyam Pouambeka*, Hubert Makomo, Ghislain Kende, Timoléon Andzi Barhé

Equipe de Chimie Organique et Analytique des Substances Bioactives, Faculté des Sciences et Techniques, Université Marien Ngouabi, Brazzaville, République du Congo BP 69

Abstract: By using the combining of N-fluorobenzenesulfonimide and H₂O, we have realized the first example of high efficient and easy hydroamination of terminal alkynes. The reaction was catalyzed by copper and the corresponding β-amino substituted styrenes have been afforded in good to excellent yields. The transformation under simple mild conditions feature a broad substrate scope, atom economy, good functional group tolerance and the simple mechanism was proposed. The different products obtained were characterized using ¹HNMR, ¹³CNMR and HRMS.

Keywords: hydroamination, β-amino substituted styrenes, N-fluorobenzenesulfonimide (NFSI), Copper-Catalyzed

Received October 19, 2023; Revised November 21, 2023; Accepted November 27, 2023

Citation: Tony Wheellyam Pouambeka, Hubert Makomo, Ghislain Kende, Timoléon Andzi Barhé, Copper-Catalyzed Hydroamination of Terminal Alkynes by Combining N-fluorobenzenesulfonimide and H2O: Synthesis of β-amino Substituted Styrenes. World Journal of Organic Chemistry, 10 (1). 4-19. January 2023. doi:10.12691/wjoc-10-1-2

1. Introduction

The formation of carbon nitrogen bond using available and inexpensive compounds is essential in organic chemistry and is of great importance in the pharmaceutical and biological fields [1-4].The important of nitrogen-containing compounds is one of the raisons that led the chemists to develop new C−N bond-forming transformations [5,6]. In particular, amination of unsaturated carbon-carbon bonds, such as aminooxygenation [7], aminoﬂuorination [8], carboamination [9], thiocyanation-amination [10], aminocyanation [11], aminoalkylation [12] and hydroamination [13] of alkenes, allenes, and alkynes, has emerged as a powerful tool for C-N bond formation. Among those transformations, the alkyne hydroamination reaction constitutes a powerful synthetic procedure with the potential to gain access to amine products which are widely featured in pharmaceutically active compounds [14-16]. This reaction is much more efficient when catalyzed by a transition metal [17]. In this contexe, Kozlov and all reported in 1936 the first mercury-catalyzed hydroamination, but the toxicity of mercury showed the ineffectiveness of this method [18]. Further, Christina Erken and co-woker reported the hydroaminaion of aromatic alkynes to imines catalyzed by Pd(II)-Anthrophos complexes (Figure 1a) [19]. The complexity of tridentate ligand limits this reaction. To all these problems is added that of origin of the nitrogen source during the formation of C−N bond. In the past several decades, different kinds of nitrogen sources have been used for the constraction of C−N bond [20]. The NFSI can be used as an efficient nitrogen source in the case of amination. He also used as a strong efficient oxidant in transition-metal-catalyzed transformation to produce high-oxidation state metal complexes [21]. Ainsi, in 2012, our group developed palladium-catalyzed allylic C–H amination of alkenes with N-ﬂuorodibenzenesulfonimide. In this reaction, water played an important [22]. Recently, the group of Bi reported silver-catalyzed hydroazidation of Terminal Alkynes by combining a nitrogen source sach as TMS‑N₃ and H₂O for the Synthesis of Vinyl Azides [23]. These results demonstrated that an appropriate amount of H₂O was essential for the hydroamination of terminal alkynes with TMS-N₃. However, transition-metal-catalyzed hydroamination of alkynes by using a combination of a nitrogen source and H₂O remains an area of study for organic synthesis. In this context, we report Copper-Catalyzed Hydroamination of Terminal Alkynes by Combining N-fluorobenzenesulfonimide as a nitrogen source and H₂O to synthesis of β-amino substituted styrenes (Figure 1b).

Figure 1. Catalytic Hydroamination of alkynes

2. Experimental Procedures

2.1. Materials

All reactions were carried out under air atmosphere and monitored by Analytical thin-layer chromatography (TLC) with Machery-Nagel 0.20 mm silica gel 60 plates. Flash column chromatography was carried out using 300-400 mesh silica gel at increased pressure. ¹H NMR spectra were recorded at ambient temperature on a Varian 400 MHz, ¹³C NMR spectra were recorded at ambient temperature on a Varian 125 MHz and TMS as internal standard. Melting points were obtained with a micro melting point XT4A Beijing Keyi. Chemical shifts for 1H NMR were described in parts per million relative to internal standard TMS (0 ppm for H1) and CDCl₃ (77.0 ppm for 13C). High resolution mass spectra were recorded on Bruck microtof. Coupling Constants (J) were then expressed in Hz. The signals have been described according to the following rule: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, br = broad. All chemicals and solvents were purchased from commercial source and used as received.

2.2. General Procedure for the Synthesis of Compounds

Ethynylbenzene 1a (25.5 mg, 0.25 mmol), NFSI (157.5 mg, 0.5 mmol), CuCl (2.5 mg, 0.025 mmol) and H₂O (13.5 mg 0.75 mmol) were placed in a round-bottomed flask containing a magnetic stirrer under air atmosphere. 3 mL of dichloromethane (DCM) was dissolved. The mixture was then stirred at 60 ºC for 2 hours and monitored by TLC. After, the aqueous layer was extracted with dichloromethane (5.0 mLx3) and the organic layers were combined, washed with water and dried over anhydrous Na₂SO₄. The organic layer was filtered, concentrated by rotary evaporation and purified by flash colunm chromatography on silicate gel as solid phase and petroleum/ethyl acetate (25:1, v:v) as the eluent to give compound 2a (84.20 mg, 85 % ) as a white solid.

2.3. Characterization Data of Compound 2

(E)-N-(phenylsulfonyl)-N-styrylbenzenesulfonamid (2a)

White solid (84.20 mg, 85%); mp: 171-173 °C; 1H NMR (400 MHz; CDCl3): δ = 6.54 (d, J = 13.6 Hz, 1H, =CH-N), 6.66 (d, J = 13.6 Hz, 1H, Ar-CH=), 7.31 – 7.38 (m, 5H, Ar-H), 7.56 (t, J = 8.0 Hz, 4H,), 7.67 (t, J = 7.6 Hz, 2H), 8.00 (dd, J12= 1.2 Hz, J13= 8.8 Hz, 4H). 13C NMR (125 MHz; CDCl3): δ = 119.4, 127.2, 128.1, 128.8, 129.1, 129.4, 133.7, 134.0, 139.1, 139.4. HRMS (ESI-TOF) calcd for C20H17NNaO4S2, [M+Na]+ 422.0497 Found 422.0512.

(E)-N-(4-chlorostyryl)-N-(phenylsufonyl)benzenesulfonamide (2b)

White solid (63.32 mg, 78%); mp: 153-156 °C; ¹H NMR (400 MHz, CDCl₃): δ = 6.51 (d, J = 13.6 Hz, 1H), 6.65 (d, J = 13.6 Hz, 1H), 7.56 – 7.33 (m, 4H), 7.67 (t, J = 8.0 Hz, 4H), 7.69 (t, J = 7.2 Hz, 2H), 7.99 (d, J = 7.6 Hz, 4H). NMR (125 MHz; CDCl₃): δ = 120.0, 128.1, 128.4, 129.0, 129.1, 132.2, 134.1, 135.2, 137.4, 139.4. HRMS (ESI-TOF) calcd for C₂₀H₁₆ClNNaO₄S₂, [M+Na]⁺ 456.0107 Found 456.01406.

(E)-N-(4-fluorostyryl)-N-(phenylsufonyl)benzenesulfonamide (2c)

White solid (64.21 mg, 72%); mp: 155-157 °C; ¹H NMR (400 MHz, CDCl₃): δ= 6.45 (d, J = 13.6 Hz, 1H), 6.65 (d, J = 14.0 Hz, 1H), 7.04 (t, J = 8.4 Hz, 2H), 7.32 – 7.35 (m, 2H), 7.57 (t, J = 8.0 Hz, 4H), 7.69 (t, J = 7.2 Hz, 2H), 7.99 (d, J = 7.2 Hz, 4H). NMR (125 MHz; CDCl₃): δ = 115.8, 116.0, 119.1, 128.2, 128.9, 129.1, 134.0, 137.9, 139.4, 141.9 HRMS (ESI-TOF) calcd for C₂₀H₁₆FNNaO₄S₂, [M+Na]⁺ 440.0402 Found 440.0407.

(E)-N-(4-bromostyryl)-N-(phenylsufonyl)benzenesulfonamide (2d)

White solid (45.11 mg, 67%); mp: 152-154 °C; ¹H NMR (400 MHz, CDCl₃): δ = 6. 52 (d, J = 13.6 Hz, 1H), 6.65 (d, J = 13.6 Hz, 1H), 7.22 (d, J = 8.4 Hz, 2H), 7.48 (d, J = 8.4 Hz, 2H), 7.57 (t, J = 8.4 Hz, 4H), 7.67 (t, J = 7.2 Hz, 2H), 7.99 (d, J = 7.2 Hz, 4H). NMR (125 MHz; CDCl₃): δ = 119.4, 127.2, 128.2, 128.8, 129.1, 129.4, 133.7, 134.0, 139.1, 139.5. HRNS (ESI-TOF) calcd for C₂₀H₁₇BrNO₄S₂, [M+H]⁺ 477.9777; Found 477.9288.

(E)-N-(3-bromostyryl)-N-(phenylsufonyl)benzenesulfonamide (2e)

White solid (35.10 mg, 52%); mp: 150-151 °C; ¹H NMR (400 MHz, CDCl₃): δ = 6.56 (d, J = 14.0 Hz, 1H), 6.65 (d, J = 14.0 Hz, 1H), 7.22 – 7.27 (m, 2H), 7.46 (d, J = 7.6 Hz, 1H), 7.51 (s, 1H), 7.58 (t, J = 8.0 Hz, 4H), 7.69 (t, J = 7.2 Hz, 2H), 8.00 (dd, J₁₂ = 1.6 Hz, J₁₃ = 8.0 Hz, 4H) NMR (125 MHz; CDCl₃): δ =120.8, 122.9, 125.8, 128.1, 129.1, 129.8, 130.3, 132.1, 134.1, 135.8, 136.8, 139.3. HRMS (ESI-TOF) calcd for C₂₀H₁₆BrNNaO₄S₂, [M+Na]⁺ 499.9596 Found 499.9589.

(E)-N-(4-methoxystyryl)-N-(phenylsufonyl)benzenesulfonamide (2f)

White solid (68.78 mg, 83%); mp: 130-132°C; ¹H NMR (400 MHz, CDCl₃): δ = 3.82 (s, 3H), 6.37 (d, J = 13.6 Hz, 1H), 6.60 (d, J = 13.6 Hz, 1H), 6.87 (d, J = 8.8 Hz, 2H), 7.30 (d, J = 8.8 Hz, 2H), 7.56 (t, J = 8.0 Hz, 4H), 7.67 (t, J = 7.2 Hz, 2H), 7.99 (d, J = 7.6 Hz, 4H). NMR (125 MHz; CDCl₃): δ = 55.4, 114.2, 117.0, 126.3, 128.2, 128.7, 129.1, 133.9, 139.3, 139.5, 160.5. HRMS (ESI-TOF) calcd for C₂₁H₁₉NNaO₅S₂, [M+Na]⁺ 452.0602 Found 452.0613.

(E)-N-(2,4-dimethylstyryl)-N-(phenylsufonyl)benzenesulfonamide (2g)

White solid (61.97 mg, 74%); mp: 152-154 °C; ¹H NMR (400 MHz, CDCl₃): δ =2.18 (s, 3H), 2.31 (s, 3H), 6.33 (d, J = 13.6 Hz, 1H), 6.84 (d, J = 13.6 Hz, 1H), 6.99 (d, J = 5.6 Hz, 2H), 7.29 (d, J= 8.0 Hz, 1H), 7.53 – 7.57 (m, 4H), 7.64 – 7.69 (m, 2H), 8.00 (d, J = 7.2 Hz, 4H) NMR (125 MHz; CDCl₃): δ = 19.6, 21.2, 119.3, 126.2, 126.9, 128.1, 129.1, 129.9, 131.3, 133.9, 136.5, 138.0, 139.4, 139.5. HRMS (ESI-TOF) calcd for C₂₂H₂₂NO₄S₂, [M+H]⁺ 428.0985 Found 428.0905.

(E)-N-(4-methylstyryl)-N- (phenylsufonyl)benzenesulfonamide (2h)

White solid (74.43 mg, 82%); mp: 133-135 °C; ¹H NMR (400 MHz, CDCl₃): δ = 2.36 (s, 3H), 6.46 (d, J = 13.6 Hz, 1H), 6.64 (d, J = 14.0 Hz, 1H), 7.15 (d, J = 7.6 Hz, 2H), 7.25 (d, J = 7.2 Hz, 2H), 7.56 (t, J = 8.0 Hz, 4H), 7.67 (t, J = 7.2 Hz, 2H), 7.99 (d, J = 8.0 Hz, 4H). NMR (125 MHz; CDCl₃): δ = 21.3, 118.3, 127.2, 128.2, 129.0, 129.5, 130.9, 133.9, 139.3, 139.5, 139.6. HRMS (ESI-TOF) calcd for C₂₁H₁₉NNaO₄S₂, [M+Na]⁺ 436.0653 Found 436.0672.

(E)-N-(2-methylstyryl)-N-(phenylsufonyl)benzenesulfonamide (2i)

White solid (72.62 mg, 80%); mp: 131 – 133 °C; ¹H NMR (400 MHz, CDCl₃): δ = 2.35 (s, 3H), 6.51 (d, J = 13.6 Hz, 1H), 6.65 (d, J = 14.0 Hz, 1H), 7.15-7.19 (m, 3H), 7.24 (t, J = 6.4 Hz, 1H), 7.57 (t, J = 8.0 Hz, 4H), 7.65 – 7.69 (m, 2H), 8.00 (d, J = 7.2 Hz, 4H). NMR (125 MHz; CDCl₃): δ = 21.3, 119.1, 124.4, 127.8, 128.0, 128.1, 128.7, 129.1, 133.6, 133.9, 136.0, 138.5, 139.3. HRMS (ESI-TOF) calcd for C₂₁H₁₉NNaO₄S₂, [M+Na]⁺ 436.0653 Found 436.0609.

(E)-N-(4-(ter-butyl)styryl)-N-(phenylsufonyl)benzenesulfonamide (2j)

White solid (63.14 mg, 86 mp: 137 – 138 °C; ¹H NMR (400 MHz, CDCl₃): δ = 1.32 (s, 9H), 6.49

(d, J = 13.6 Hz, 1H), 6.66 (d, J = 13.6 Hz, 1H), 7.30 (d, J = 8.4 Hz, 2H), 7.38 (d, J = 8.4 Hz, 2H), 7.57 (t, J = 8.0 Hz, 4H), 7.64 – 7.69 (m, 2H), 8.00 (dd, J12 = 1.6 Hz, J13 = 8.0 Hz, 4H). ¹³C NMR (125 MHz; CDCl₃): δ = 31.2, 34.8, 118.5, 125.7, 127.0, 128.1, 129.1, 130.9, 133.9, 139.1, 139.5, 152.8. HRMS (ESI-TOF) calcd for C₂₄H₂₆NO₄S₂, [M+H]+ 456.1298 Found 456.1292.

3. Results and Discussion

Table 1. Optimization of reaction Conditions

Table 2. Scope of Copper-calalyzed Hydroamination of Terminal Alkynes

In the absence of metal and water (Table 1, entry 1), no product was obtained. The use of copper Cu(OAc)2 as a catalyst in the absence of water (Table 1, entry 2) had no effect on the reaction. The combination of copper Cu(OAc)2 and an equivalent of water in the presence of dichloromethane at 60˚C (Table 1, entry 3) made it possible to obtain for the first time the desired product 2a in 21% yield. Different kind of copper such as CuSO4, CuCl2, CuBr and CuCl were used during this reaction (Table 1, entries 4-7), in the presence of DCM and an equivalent of water; the desired product 2a was obtained in 58% yield by using CuCl as catalyst. When we increased water, from 2 equivalents to 3 equivalents, under the same conditions (Table 1, entry 7), the desired product 2a was obtained in 60 % and 85 % yields, respectively. Several types of solvents were also used during this series such as: DMF, THF, DCE, Toluène, DMSO and Dioxane (Table 1, entries 10-15); only the DCE clearly gave product 2a in 79 % yield (Table 1, entry 12). Temperature also played a fairly important role in this reaction. When the reaction temperature was increased from 80˚C to 100˚C, we found a drop in the yield of product 2a from 60 % to 50 % respectively (Table 1, entries 16-17). With a decrease in temperature, no products were obtained.

Base on the optimization of this reaction in (Table 1, entry 9), the scope of copper-catalyzed Hydroamination of Terminal Alkynes was examined in a series of ethynylbenzene and the results are summarized in Table 2. The monohalogenated derivatives in the para position of the benzene ring such as 1b, 1c, and 1d were satisfactory during this reaction, giving the products 2b, 2c and 2d in yields of 78 %, 72 % and 67 % yields, respectively. When bromine is used in meta position (1e), we obtained product 2e with a slightly lower yield than products 2b, 2c and 2d. This reduction in yield can be explained by the delocalization of the benzene nucleus caused by the halogens in the para or meta position. The compounds 1f, 1g, 1h, 1i and 1j carrying electron donating groups such as methoxy, methyl and tertiobethyl (tBu) were also satisfactory during this transformation, giving the products 2(f-j) in 80 %, 74 %, 82 %, 80 % and 86% yields, respectively.

4. Proposed Mechanism

We proposed a plausible reaction radical mechanism for this transformation, in which the Cu(I) species reacted with NFSI to form the species Cu(III) A which can be in equilibrium with a radical species Cu(II) B. The radical addition reaction between the radical species Cu(II) B with a terminal alkyne 1leads to species Cu(II) D avec the radical intermediate C [24-28]. Afterwards, la combinaison entre species C and D in the presence of water leads to the desired product 2 and also the complex E which subsequently undergoes decomposition to give hypofluorous acid and generated the catalyst Cu(I).

Figure 2. Proposed Mechanism for the synthesis of compounds 2

¹H and ¹³C Spectra of New Compounds

Figure 3. ¹HNMR spectrum of compound 2a

Figure 4. ¹³C NMR spectrum of compound 2a

Figure 5. ¹HNMR spectrum of compound 2b

Figure 6. ¹³CNMR spectrum of compound 2b

Figure 7. ¹HNMR spectrum of compound 2c

Figure 8. ¹³CNMR spectrum of compound 2c

Figure 9. ¹HNMR spectrum of compound 2d

Figure 10. ¹³CNMR spectrum of compound 2d

Figure 11. ¹HNMR spectrum of compound 2e

Figure 12. ¹³CNMR spectrum of compound 2e

Figure 13. ¹HNMR spectrum of compound 2f

Figure 14. ¹³CNMR spectrum of compound 2f

Figure 15. ¹HNMR spectrum of compound 2g

Figure 16. ¹³CNMR spectrum of compound 2g

Figure 17. ¹HNMR spectrum of compound 2h

Figure 18. ¹³CNMR spectrum of compound 2h

Figure 19. ¹HNMR spectrum of compound 2i

Figure 20. ¹³CNMR spectrum of compound 2i

Figure 21. ¹HNMR spectrum of compound 2j

Figure 22. ¹³CNMR spectrum of compound 2j

5. Conclusion

In conclusion, we have established a highly eﬃcient protocol for the synthesis of β-amino substituted styrenes 2 via a terminal alkynes with N-fluorobenzenesulfonimide (NFSI) as a nitrogen source and also an oxidant in the presence of copper as a catalyst, which would be useful in organic synthesis and medicinal chemistry. In this transformation, water played a very important role in the fixation of a hydrogen atom at the level of the triple bond of a terminal alkyne in the anti-markovnikov position. This novel strategy provides a mild and eﬃcient method for to realize a C-N bond. The reaction shows high eﬃciency and selectivity, as well as a broad substrate scope. Further, mechanistic studies and applications of this transformation are underway in our laboratory.

Author Information

*Corresponding Author: Tony Wheellyam Pouambeka: tonywheellyam@yahoo.fr

Hubert Makomo :

Ghislain Kende:

Timoléon Andzi Barhé:

ACKNOWLEDGEMENTS

This work has been partially supported by the key laboratory or organic functional molecular design and synthesis, faculty of chemistry, Northeast Normal University and Marien Ngouabi University. Prof. Zhan Qian is greatly acknowledged for helpful comments and suggestions.

References

[1]   | LI, X., Yuan X., Hu J., et al. Radical Decarboxylative Carbon–Nitrogen Bond Formation. Molecules. 2023, 28(10): 4249.
[2]   | Goh J., Ong S. K., Tan Y. S., Loh T. P. Catalyst-free C–N bond formation under biocompatible reaction conditions. Green Chemistry. 2022, 24(8): 3321-3325.
[3]   | Bariwal J., Van der Eycken E. C–N bond forming cross-coupling reactions: an overview. Chem Soc Rev. 2013, 42(24): 9283-9303.
[4]   | Zarnegar Z., Alizadeh R., Ahmadzadeh M., Safari J. C-N bond formation in alicyclic and heterocyclic compounds by amine-modified nanoclay. J. Mol. Struct. 2017, 1144, 58-65.
[5]   | Zheng Y. N., Zheng H., Li T., Wei W. T. Recent Advances in Copper‐Catalyzed C− N Bond Formation Involving N‐Centered Radicals. Chem Sus Chem. 2021, 14(24): 5340-5358.
[6]   | Ma D., Zhai S., Wang Y., Liu A., Chen C. Synthetic approaches for C-N bonds by TiO2 photocatalysis. Front. Chem. 2019, 7, 635.
[7]   | McNichol C. P., DeCicco E. M., Canfield A. M., Carstairs D. P., Paradine S. M. (2023). Copper-Catalyzed Aerobic Aminooxygenation of Cinnamyl N-Alkoxycarbamates via Substrate-Promoted Catalyst Activation. ACS Catalysis. 2023, 13(10): 6568-6573.
[8]   | Zhao J., Jiang M., Liu J. T. Transition metal-free aminofluorination of β, γ-unsaturated hydrazones: base-controlled regioselective synthesis of fluorinated dihydropyrazole and tetrahydropyridazine derivatives. Org. Chem. Front. 2018, 5(7): 1155-1159.
[9]   | Nanda S. K., Mallik R. 1, 2-Difunctionalizations of alkynes entailing concomitant C–C and C–N bond-forming carboamination reactions. RSC advances. 2022, 12(10): 5847-5870.
[10]   | Wu H., Shao C., Wu D., Jiang L., Yin H., Chen F. X. Atom-Economical Thiocyanation-Amination of Alkynes with N-Thiocyanato-Dibenzenesulfonimide. J. Org. Chem. 2021, 86(7): 5327-5335.
[11]   | Qian S., Lazarus T. M., Nicewicz D. A. (2023). Enantioselective Amino-and Oxycyanation of Alkenes via Organic Photoredox and Copper Catalysis. J. Am. Chem. Soc. 2023, 145(33): 18247-18252.
[12]   | Ye L. Palladium-catalyzed intramolecular aminoalkylation of unactivated alkenes for synthesis of nitrogen-containing heterocycles. HKU Theses Online. (HKUTO). 2015.
[13]   | Muller T. E., Hultzsch K. C., Yus M., Foubelo F., Tada M. Hydroamination: direct addition of amines to alkenes and alkynes. Chem. Rev. 2008, 108(9): 3795-3892.
[14]   | Escorihuela J., Lledós A., Ujaque G. Anti-Markovnikov Intermolecular Hydroamination of Alkenes and Alkynes: A Mechanistic View. Chem. Rev. 2023, 123(15): 9139-9203.
[15]   | Streiff S., Jérôme F. Hydroamination of non-activated alkenes with ammonia: a holy grail in catalysis. Chem. Soc. Rev. 2021, 50(3): 1512-1521.
[16]   | Muller T. E., Hultzsch K. C., Yus M., Foubelo F., Tada M. (2008). Hydroamination: direct addition of amines to alkenes and alkynes. Chem. Rev. 2008, 108(9): 3795-3892.
[17]   | Huang L., Arndt M., Gooßen K., Heydt H., Goossen L. J. (2015). Late transition metal-catalyzed hydroamination and hydroamidation. Chem. Rev. 2015, 115(7): 2596-2697.
[18]   | Kozlov N. S., Dinaburskaya B., Rubina T. J. J. Gen. Chem. USSR. 1936, 6, 1341.
[19]   | Erken C., Hindemith C., Weyhermüller T., Hölscher M., Werlé C., Leitner W. Hydroamination of aromatic alkynes to imines catalyzed by Pd (II)–anthraphos complexes. ACS omega. 2020, 5(15): 8912-8918.
[20]   | Zheng G., Li Y., Han J., Xiong T., Zhang Q. (2015). Radical cascade reaction of alkynes with N-fluoroarylsulfonimides and alcohols. Nat. Commun. 2015, 6(1): 7011.
[21]   | Li Y., Zhang Q. N-Fluorobenzenesulfonimide: an efficient nitrogen source for C–N bond formation. Synthesis. 2014, 159-174.
[22]   | Xiong T., Li Y., Mao L., Zhang Q. Palladium-catalyzed allylic C–H amination of alkenes with N-fluorodibenzenesulfonimide: water plays an important role. Chem Commun.2012, 48(16): 2246-2248.
[23]   | Liu Z., Liao P., Bi X. (2014). General silver-catalyzed hydroazidation of terminal alkynes by combining TMS-N3 and H2O: synthesis of vinyl azides. Org. let. 2014, 16(14): 3668-3671.